The Boyfriend shape is everything you love about a man's shirt, cut slimmer to flatter a woman. It has a slightly oversized collar and cuffs, longer tail, and front pocket for receipts, bobby pins, or an emergency breath mint. Tuck it in or don't — we love it worn out with the hem out over trousers, jeans of all kinds, short skirts, or cutoff shorts. This one's made up in a menswear-feeling, awning-striped poplin from Portugal.